Coatings used for painting motor vehicles and repairing the original paint are required to have good physical properties such as hardness, mechanical strength, and resistance to water, acids, and solvents. The coatings are also required to have good appearance properties, which means that films must be smooth and have a high gloss and high distinctness of image (DOI). It is also desirable that all properties be retained under prolonged outdoor weathering.
For environmental reasons, it is required to use a coating composition which can be applied easily using spray application at a low volatile organic content (VOC). Coatings with a lower organic solvent content emit lower levels of solvent when they are used and so the atmosphere becomes less polluted.
One way to achieve a lower solvent content is to use so-called high-solids compositions. Such compositions comprise a relatively high level of non-volatile materials, such as film forming polymer, pigments and fillers, and a relatively low level of organic solvent. A problem when formulating high-solids coating compositions is that such compositions have an unacceptably high viscosity due to the high molecular weight of the conventional film forming polymer. The high viscosity gives rise to problems in spray application with poor paint atomization and poor flow-out and, consequently, low gloss levels and poor appearance.
The use of low-molecular weight film forming polymers, which results in adequate application viscosities, has as a disadvantage that the resulting coating is soft and marks easily. The hardness build-up of the coating is therefore unacceptable.
Another way to reduce the amount of volatile organic compounds in coating compositions is the use of reactive diluents. Examples of reactive diluents include aldimines and ketimines. In EP-A-0 686 654 such compounds are discussed. Other reactive diluents, such as oxazolidines, are mentioned but it is stated that they have limited utility as a sole reaction partner with isocyanate because of generally slow setting film properties.
Aldimines are used as reactive diluents for low VOC paint systems. These diluents are commercially available and use of such aldimines is referred to in U.S. Pat. No. 5,214,086 and EP-A-0 686 654. In general these reactive diluents offer good cure and hardness development. However, they are known to cause skin irritation and to cause adhesion failure when applied in low VOC clearcoats.
Bicyclic oxazolidines are also used as reactive diluents for low VOC paint systems. These diluents are commercially available and use of such bicyclic oxazolidines are referred to in WO 95/14528. In general, these reactive diluents offer good durability and color stability and low toxicity. However, compositions based on bicyclic oxazolidines may exhibit an unacceptably long time to cure.
Monocyclic oxazolidines are also used as reactive diluents for low VOC paint systems. Coating compositions based on monocyclic oxazolidines are also referred to in EP 0 499 188 A1. Monocyclic oxazolidines and dimers of the same are commercially available. Coating compositions based on monocyclic oxazolidines may exhibit a loss of adhesion over time.
While the use of mono- or bi-cyclic oxazolidines has been described (see, e.g., U.S. Pat. No. 5,126,421), nowhere is there described the use of both monocyclic and bicyclic oxazolidines. Wo 92/13907 refers to the use of monocyclic and bicyclic oxazolidines (page 7, lines 20-21), but this reference relates to the use of these compounds in the alternative and does not disclose a mixture of the two oxazolidines.
Surprisingly it was found that the use of mixtures of bicyclic and monocyclic oxazolidines as reactive diluents in low VOC coatings provide properties that can compete with those of imines, but without loss of adhesion.